Cyclopropylamine → HCID 32917957, compound

HRID 1845148Notes

Reaction equation

HRID 1845148 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12](=[O:14])(=[O:13])[NH:19][CH:16]1[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 18071846methyl 4-chloro-3-(chlorosulfonyl)benzoate

Product 1

HCID 32917957HCID 32917957, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A round bottom flask was charged with methyl 4-chloro-3-(chlorosulfonyl)benzoate (12.0 g, 44.32 mmol) and 1,4-dioxane (100 mL) at 0° C. Cyclopropyl amine (9.31 mL, 137.8 mmol) was added dropwise and the mixture was stirred at that temperature for 3 h. The solvent was removed and the residue was treated with EtOAc. The organic phase was washed with brine, dried, and concentrated to get the title compound (4.5 g, 32% yield).

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with EtOAc
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e525f33a2ede44698c50561bd5697ec1
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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